Dimethylamine → N,N-Dimethyl-1,4-dioxaspiro[4.5]decan-8-amine

HRID 440929노트

반응식

HRID 440929 반응식
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]2)[O:3][CH2:2]1.[CH3:12][NH:13][CH3:14].C([BH3-])#N.[Na+]>C(O)(=O)C>[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][CH:7]([N:13]([CH3:14])[CH3:12])[CH2:6][CH2:5]2)[O:3][CH2:2]1

참가 물질

5

반응물 3

HCID 674DimethylamineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 361167N,N-Dimethyl-1,4-dioxaspiro[4.5]decan-8-amine수율 85%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

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온도
0 °C

실험 절차

To a solution of 5.0 gm (32 mMol) 1,4-cyclohexanedione mono-ethylene ketal and 10.80 gm (240 mMol) dimethylamine were added 2.0 mL acetic acid and the mixture was stirred at 0° C. for 1.5 hours. To this solution were then added 3.62 gm (58 mMol) sodium cyanoborohydride and the reaction stirred for an additional hour at ambient. The pH of the reaction mixture was adjusted to ~7 with 16 mL acetic acid and stirred 18 hours at ambient. The volatiles were removed under reduced pressure and the residue dissolved in cold 5% tartaric acid solution and then the aqueous phase was made basic with 5N sodium hydroxide. This aqueous phase was extracted well with dichloromethane. These organic extracts were combined and concentrated under reduced pressure to give 5.04 gm (85%) of the title compound as an oil.

후처리

  1. stirringthe reaction stirred for an additional hour at ambient
  2. stirringstirred 18 hours at ambient
  3. customThe volatiles were removed under reduced pressure
  4. dissolutionthe residue dissolved in cold 5% tartaric acid solution
  5. extractionThis aqueous phase was extracted well with dichloromethane
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-69cb40557ca24c0992fe10606ab4c95c
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521196

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